1-[(Benzyloxy)carbonyl]-2-indolinecarboxylic acid

Base Information

• Chemical Name: 1-[(Benzyloxy)carbonyl]-2-indolinecarboxylic acid
• CAS No.: 117483-89-3
• Molecular Formula: C17H15 N O4
• Molecular Weight: 297.31
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID201347562
• Mol file: 117483-89-3.mol

Synonyms:117483-89-3;1-[(Benzyloxy)carbonyl]-2-indolinecarboxylic acid;1-((Benzyloxy)carbonyl)indoline-2-carboxylic acid;1-phenylmethoxycarbonyl-2,3-dihydroindole-2-carboxylic Acid;1-[(benzyloxy)carbonyl]-2,3-dihydro-1H-indole-2-carboxylic acid;2,3-Dihydro-1H-indole-1,2-dicarboxylic acid 1-benzyl ester;Oprea1_399927;SCHEMBL1000224;BSOYWTITVKXHLM-UHFFFAOYSA-N;DTXSID201347562;MFCD02682032;AKOS015912184;4-NITRO-PHENYLALANINEMETHYLESTER;SB64918;SB65616;MS-22137;FT-0607080;1-benzyloxycarbonyl-2-indoline carboxylic acid;1-(benzyloxycarbonyl)indoline-2-carboxylic acid;EN300-103751;1-((Benzyloxy)carbonyl)indoline-2-carboxylicacid;Z335079884;1-[(benzyloxy)carbonyl]-2-indolinecarboxylic acid, AldrichCPR;1H-Indole-1,2-dicarboxylicacid,2,3-dihydro-,1-(phenylmethyl)ester

Chemical Property of 1-[(Benzyloxy)carbonyl]-2-indolinecarboxylic acid

Chemical Property:

• Vapor Pressure: 8.59E-11mmHg at 25°C
• Melting Point: 103-105掳C
• Boiling Point: 499.4°Cat760mmHg
• PKA: 3.85±0.20(Predicted)
• Flash Point: 255.8°C
• PSA: 66.84000
• Density: 1.35g/cm³
• LogP: 2.90410
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 297.10010796
• Heavy Atom Count: 22
• Complexity: 419

Purity/Quality:

98%Min ^*data from raw suppliers

1-[(Benzyloxy)carbonyl]-2-indolinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(N(C2=CC=CC=C21)C(=O)OCC3=CC=CC=C3)C(=O)O
• Uses: 1-[(Benzyloxy)carbonyl]-2-indolinecarboxylic Acid is a reagent in the preparation of dihydroisoxanzoles derivatives transglutaminase 2 enzyme inhibitor.

Technology Process of 1-[(Benzyloxy)carbonyl]-2-indolinecarboxylic acid

There total 1 articles about 1-[(Benzyloxy)carbonyl]-2-indolinecarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

indolin-2-yl carboxylic acid (16851-56-2,78348-24-0) + benzyl chloroformate (501-53-1,94274-21-2) → 1-benzyloxycarbonyl-2,3-dihydroindole-2-carboxylic acid (117483-89-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 4h;

DOI:10.1021/acs.joc.5b02532

Reference yield: 90.0%

1-benzyloxycarbonyl-2,3-dihydroindole-2-carboxylic acid (117483-89-3) + 8-amino quinoline (578-66-5) → benzyl 2-(quinolin-8-ylcarbamoyl)indoline-1-carboxylate

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 12h;

DOI:10.1039/c9ob00393b

Reference yield: 71.0%

1-benzyloxycarbonyl-2,3-dihydroindole-2-carboxylic acid (117483-89-3) + ethyl acetate n-hexane + chloroformic acid ethyl ester (541-41-3) + (3S,4S)-3-benzyloxycarbonylamino-4-acetoxy-azetidin-2-one (75666-47-6) + amino-4-acetoxy-azetidin-2-one (101651-14-3) → (3S,4S)-3-(1-N-benzyloxycarbonyl-2-indolinecarbonyl)-amino-4-acetoxy-azetidin-2-one (205493-74-9)

Guidance literature:

With hydrogen; triethylamine; palladium on activated carbon; In chloroform; ethyl acetate;

upstream raw materials:

indolin-2-yl carboxylic acid

benzyl chloroformate

Downstream raw materials:

(3S,4S)-3-(1-N-benzyloxycarbonyl-2-indolinecarbonyl)-amino-4-acetoxy-azetidin-2-one

Benzyl 2-(4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl) [1,2,4]triazol-3-ylmethylcarbamoyl)-2,3-dihydroindole-1-carboxylate

benzyl 2-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)indoline-1-carboxylate

benzyl 2-(2-amino-3-carbamoylphenylcarbamoyl)indoline-1-carboxylate

Refernces

• 1、 -. "Aromatic pyrrolidine amide prolyl endopeptidase inhibitors". . . Retrieved 2008/06/13.